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Multiple monolithic fibers modified with a molecularly imprinted polymer for solid phase microextraction of sulfonylurea herbicides based on boron-nitrogen interaction

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Abstract

This study describes a highly selective, sensitive and eco-friendly method for the determination of sulfonylurea herbicides (SUHs) in soya milk and grape juice samples. The SUHs can be extracted selectively and effectively by using molecularly imprinted multiple monolithic fibers (BNMIP/MMF) that undergo boron-nitrogen interactions with the SUHs. The sorbent can be fabricated by in-situ polymerization using triflusulfuron-methyl (TSM) as the template, and 1-vinyl-3-octylimidazolium tetrafluoroborate as the functional monomer. Results indicate that the boron-nitrogen interaction plays an important role in the selective extraction of TSM and its structural analogues. The recognition coefficient of BNMIP/MMF for TSM was as high as 8.1. Following elution with the binary solution of acetonitrile/formic acid (99.5/0.5), the SUHs were quantified by HPLC with diode array detection. Under the most favorable conditions, the limits of detection (S/N = 3) for SUHs in spiked soya milk and grape juice samples ranged between 14–58 ng·L−1 and 46–91 ng·L−1, respectively. Additional merits include high selectivity, wide linear ranges, good precision, low consumptions of sample and organic solvent. In the analysis of SUHs in real samples, the recoveries at different fortified concentrations varied from 75.2 to 102%, and the relative standard deviations (n = 3) were in the range of 1.8–9.2%.

Schematic presentation of the effect of the concentration of tetrafluoroborate on the extraction selectivity of sulfonylurea herbicides (SUHs) by molecularly imprinted multiple monolithic fibers (BNMIP/MMF).

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References

  1. Sarmah AK, Sabadie J (2002) Hydrolysis of sulfonylurea herbicides in soils and aqueous solutions: a review. J Agric Food Chem 50(22):6253–6265

    Article  CAS  Google Scholar 

  2. Carles L, Joly M, Bonnemoy F, Leremboure M, Batisson I, Besse-Hoggan P (2017) Identification of sulfonylurea biodegradation pathways enabled by a novel nicosulfuron-transforming strain Pseudomonas fluorescens SG-1: toxicity assessment and effect of formulation. J Hazard Mater 324:184–193

    Article  CAS  Google Scholar 

  3. Heine S, Schild F, Schmitt W, Krebber R, Gorlitz G, Preuss TG (2016) A toxicokinetic and toxicodynamic modeling approach using Myriophyllum spicatum to predict effects caused by short-term exposure to a sulfonylurea. Enviorn Toxicol Chem 35(2):376–384

    Article  CAS  Google Scholar 

  4. Yang JH, Cui CX, Qu LB, Chen J, Zhou XM, Zhang YP (2018) Preparation of a monolithic magnetic stir bar for the determination of sulfonylurea herbicides coupled with HPLC. Microchem J 141:369–376

    Article  CAS  Google Scholar 

  5. Daniel D, dos Santos VB, Vidal DTR, do Lago CL (2015) Determination of halosulfuron-methyl herbicide in sugarcane juice and tomato by capillary electrophoresis-tandem mass spectrometry. Food Chem 175:82–84

    Article  CAS  Google Scholar 

  6. Gure A, Lara FJ, Garcia-Campana AM, Megersa N, del Olmo-Iruela M (2015) Vortex-assisted ionic liquid dispersive liquid-liquid microextraction for the determination of sulfonylurea herbicides in wine samples by capillary high-performance liquid chromatography. Food Chem 170:348–353

    Article  CAS  Google Scholar 

  7. Gure A, Lara FJ, Moreno-Gonzalez D, Megersa N, del Olmo-Iruela M, Garcia-Campana AM (2014) Salting-out assisted liquid-liquid extraction combined with capillary HPLC for the determination of sulfonylurea herbicides in environmental water and banana juice samples. Talanta 127:51–58

    Article  CAS  Google Scholar 

  8. Yan CM, Zhang BB, Liu WY, Feng F, Zhao YG, Du H (2011) Rapid determination of sixteen sulfonylurea herbicides in surface water by solid phase extraction cleanup and ultra-high-pressure liquid chromatography coupled with tandem mass spectrometry. J Chromatogr B 879(30):3484–3489

    Article  CAS  Google Scholar 

  9. Jakubus A, Paszkiewicz M, Stepnowski P (2017) Carbon nanotubes application in the extraction techniques of pesticides: a review. Crit Rev Anal Chem 47(1):76–91

    Article  CAS  Google Scholar 

  10. Lerma-García MJ, Zougagh M, Ríos A (2013) Magnetic molecular imprint-based extraction of sulfonylurea herbicides and their determination by capillary liquid chromatography. Microchim Acta 180:363–370

    Article  Google Scholar 

  11. Miao SS, Wu MS, Zuo HG, Jiang C, Jin SF, Lu YC, Yang H (2015) Core-shell magnetic molecularly imprinted polymers as sorbent for sulfonylurea herbicide residues. J Agric Food Chem 63(14):3634–3645

    Article  CAS  Google Scholar 

  12. Pei M, Zhu XY, Huang XJ (2018) Mixed functional monomers-based monolithic adsorbent for the effective extraction of sulfonylurea herbicides in water and soil samples. J Chromatogr A 1531:13–21

    Article  CAS  Google Scholar 

  13. Ma JP, Jiang LH, Wu GG, Xia Y, Lu WH, Li JH, Chen LX (2016) Determination of six sulfonylurea herbicides in environmental water samples by magnetic solid-phase extraction using multi-walled carbon nanotubes as adsorbents coupled with high-performance liquid chromatography. J Chromatogr A 1466:12–20

    Article  CAS  Google Scholar 

  14. Deng YL, Zhang RQ, Li D, Sun P, Su P, Yang Y (2018) Preparation of iron-based MIL-101 functionalized polydopamine@Fe3O4 magnetic composites for extracting sulfonylurea herbicides from environmental water and vegetable samples. J Sep Sci 41:2046–2055

    Article  CAS  Google Scholar 

  15. Yang JH, Zhou XM, Zhang YP, Chen J, Ma HW (2017) A novel method for the determination of trace sulfonylurea herbicides by introducing a hybrid stationary phase to common capillary. Adsorpt Sci Technol 35:372–385

    Article  CAS  Google Scholar 

  16. Seccia S, Albrizio S, Fidente P, Montesano D (2011) Development and validation of a solid-phase extraction method coupled to high-performance liquid chromatography with ultraviolet-diode array detection for the determination of sulfonylurea herbicide residues in bovine milk samples. J Chromatogr A 1218(9):1253–1259

    Article  CAS  Google Scholar 

  17. Zhu QZ, Haupt K, Knopp D, Niessner R (2002) Molecularly imprinted polymer for metsulfuron-methyl and its binding characteristics for sulfonylurea herbicides. Anal Chim Acta 468(2):217–227

    Article  CAS  Google Scholar 

  18. Bastide J, Cambon JP, Breton F, Piletsky SA, Rouillon R (2005) The use of molecularly imprinted polymers for extraction of sulfonylurea herbicides. Anal Chim Acta 542(1):97–103

    Article  CAS  Google Scholar 

  19. She YX, Cao WQ, Shi XM, Lv XL, Liu JJ, Wang RY, Jin F, Wang J, Xiao H (2010) Class-specific molecularly imprinted polymers for the selective extraction and determination of sulfonylurea herbicides in maize samples by high-performance liquid chromatography-tandem mass spectrometry. J Chromatogr B 878(23):2047–2053

    Article  CAS  Google Scholar 

  20. Chen CB, Yang LQ, Zhou J (2011) Trace bensulfuron-methyl analysis in tap water, soil, and soybean samples by a combination of molecularly imprinted stir bar sorption extraction and HPLC-UV. J Appl Polym Sci 122(2):1198–1205

    Article  CAS  Google Scholar 

  21. Mei M, Huang XJ, Yuan DX (2014) Multiple monolithic fiber solid-phase microextraction: a new extraction approach for aqueous samples. J Chromatogr A 1345:29–36

    Article  CAS  Google Scholar 

  22. Huang XJ, Mei M, Zhang Y, Yuan DX (2014) Preparation method for solid-phase micro-extraction fiber bundle. Chin Patent No ZL 201410122396:7

    Google Scholar 

  23. Ren LB, Liu Z, Liu YC, Dou P, Chen HY (2009) Ring-opening polymerization with synergistic co-monomers: access to a boronate-functionalized polymeric monolith for the specific capture of cis-diol-containing biomolecules under neutral conditions. Angew Chem Int Ed 48(36):6704–6707

    Article  CAS  Google Scholar 

  24. Hu HY, Zhang Y, Zhang Y, Huang XJ, Yuan DX (2014) Preparation of a new sorbent based on boronate affinity monolith and evaluation of its extraction performance for nitrogen-containing pollutants. J Chromatogr A 1342(4):8–15

    Article  CAS  Google Scholar 

  25. Kaczyński P (2017) Large-scale multi-class herbicides analysis in oilseeds by rapid one-step QuEChERS-based extraction and cleanup method using liquid chromatography-tandem mass spectrometry. Food Chem 230:411–422

    Article  Google Scholar 

  26. Rejczak T, Tuzimski T (2016) Simple, cost-effective and sensitive liquid chromatography diode array detector method for simultaneous determination of eight sulfonylurea herbicides in soya milk samples. J Chromatogr A 1473:56–65

    Article  CAS  Google Scholar 

  27. Gure A, Lara FJ, Megersa N, Olmo-Iruela MD, García-Campaña AM (2014) Dispersive liquid-liquid microextraction followed by capillary high-performance liquid chromatography for the determination of six sulfonylurea herbicides in fruit juices. Food Anal Methods 7(7):1465–1473

    Google Scholar 

  28. Ngaosi N, Seebunrueng K, Srijaranai S (2016) In-syringe reversed dispersive liquid-liquid microextraction coupled to high performance liquid chromatography for the determination of sulfonylurea herbicide residues in cereal samples. Anal Methods 8:4254–4262

    Article  CAS  Google Scholar 

  29. Liang P, Wang JJ, Liu GJ, Guan JY (2014) Determination of four sulfonylurea herbicides in tea by matrix solid-phase dispersion cleanup followed by dispersive liquid-liquid microextraction. J Sep Sci 37(17):2380–2387

    Article  CAS  Google Scholar 

  30. Liang P, Wang JJ, Liu GJ, Guan JY (2014) Determination of sulfonylurea herbicides in food crops by matrix solid-phase dispersion extraction coupled with high-performance liquid chromatography. Food Anal Methods 7(7):1530–1535

    Article  Google Scholar 

  31. Quesada-Molina C, Olmo-Iruela MD, García-Campaña AM (2010) Trace determination of sulfonylurea herbicides in water and grape samples by capillary zone electrophoresis using large volume sample stacking. Anal Bioanal Chem 397(6):2593–2601

    Article  CAS  Google Scholar 

  32. Peng Y, Xie Y, Luo J, Nie L, Chen Y, Chen LN, Du SH, Zhang ZP (2010) Molecularly imprinted polymer layer-coated silica nanoparticles toward dispersive solid-phase extraction of trace sulfonylurea herbicides from soil and crop samples. Anal Chim Acta 674(2):190–200

    Article  CAS  Google Scholar 

  33. Seebunrueng K, Santaladchaiyakit Y, Srijaranai S (2013) The simultaneous analysis of sulfonylurea herbicide residues in fruit samples using ultrasound-assisted surfactant-enhanced emulsification microextraction coupled with high-performance liquid chromatography. Anal Methods 5:6009–6016

    Article  CAS  Google Scholar 

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Acknowledgements

The work described in this article was supported by the National Natural Science Foundation of China (grant: 21577111, 21777133).

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Authors and Affiliations

  1. State Key Laboratory of Marine Environmental Science, Key Laboratory of the Ministry of Education for Coastal and Wetland Ecosystem, College of the Environment and Ecology, Xiamen University, P. O. Box 1009, Xiamen, 361005, China

    Lei Chen, Jiangyi Wu & Xiaojia Huang

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  1. Lei Chen
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  2. Jiangyi Wu
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  3. Xiaojia Huang
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Correspondence to Xiaojia Huang.

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Chen, L., Wu, J. & Huang, X. Multiple monolithic fibers modified with a molecularly imprinted polymer for solid phase microextraction of sulfonylurea herbicides based on boron-nitrogen interaction. Microchim Acta 186, 470 (2019). https://doi.org/10.1007/s00604-019-3610-7

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